5-6 Day Sail

Week Aweigh Cruises - Sample Itinerary

5 or 6 day San Juan Islands Sailing Vacations

Set sail on your ultimate fully crewed, all-inclusive San Juan sailing vacation. The San Juans are a world-class destination, considered by many to be the crown jewels of the Pacific Northwest. Only one thing could make them better: YOU! Most sailing charters adhere to rigid schedules and itineraries. When you sail with us, YOU set the schedule! Want to set sail on a Friday? A Tuesday? A Sunday? No worries! Want to sail for six days, but your travel plans only allow for five? No problem! Check your calendar and give us a call. We will usually be able to find dates to fulfill your wishes. Enjoy a private charter for four. Want a romantic getaway for just the two of you? The choice is yours!

The Ultimate Experience:
Six luxurious days sailing the San Juan Islands

San Juans Map

Call or text (541)350-4787 or email: scott@nwsailing.com

Example of a 6-Day Itinerary


Day One: Your adventure begins in Bellingham, about two hours north of Seattle or three hours from Sea-Tac International Airport. We set sail in the early afternoon, usually between 10:00 and 2:00 pm (depending on your schedule).

Your destination for today is Sucia Island. You’ll arrive at Sucia after a delightful four to six-hour sail, depending on the winds, currents, and route is chosen. You’ll likely see porpoises, seals, and sea lions along the way. This will whet your appetite for what is to come!

Your first night will be spent in one of Sucia’s seven beautiful anchorages after enjoying a gourmet dinner served aboard. While there, you’ll enjoy examining the island’s distinctive sandstone formations up close, hiking, paddling, or a bit of beachcombing in Sucia Island State Park.

Day Two: After coffee and breakfast, you’ll embark on the next leg of your adventure. Your destination for today is Garrison Bay on San Juan Island. Along the way, be on the lookout for Orcas, Humpbacks, and Minke Whales to frequent this area.

You may stop off at Roche Harbor to visit the 19-acre sculpture park, walk the docks to look at the enormous luxury yachts, peruse the work of local artists, or learn about the historic lime kilns. You’ll then continue on to your destination.

You’ll anchor in sheltered Garrison Bay within sight of English Camp National Historic Park. You’ll dine aboard, possibly with an appetizer of live oysters purchased at the Westcott Bay Shellfish Company.

While in Garrison Bay, you’ll want to visit English Camp to learn about the Pig War and possibly hike up Young Hill for its sweeping views of the islands.


Day Three: You’ll set sail for Prevost Harbor on pastoral Stuart Island, passing the historic Turn Point Light Station along the way.

A visit to Stuart Island is like going back in time! Many of the families that live there are descendants of the pioneers who settled the island. The island is off the grid, so those who require electricity must make their own.

While there, you may choose to walk to the Light Station. You may tour the restored light keeper’s quarters and the museum or simply sit on the huge verandah and put your feet up.

Along the way, you’ll see yaks (yes, yaks!) grazing at Ericksen Farm, which has been in operation for over a hundred years. Another point of interest is the one-room school house which was in operation until just a few years ago.

You can also buy a locally designed souvenir from one of the treasure chests found around the island which offer their wares on the honor system. Simply take what you want and pay when you get home. Prevost Harbor is another great place to paddle.

Day Four: Your next destination is bustling Friday Harbor on San Juan Island.

Along the way, you may sail past Spieden Island, where you will likely see herds of exotic animals roaming the savanna-like south side of the island. You’ll also pass Yellow Island, Owned by the Nature Conservancy, on which the area indigenous people cultivated and harvested camas roots in days gone by.

You’ll continue down San Juan Channel to Friday Harbor, the hub of island activity. Here Diminuendo will tie up dockside overnight. Many art galleries, museums, scooter rentals, and tours are offered just a short walk from the marina. You’ll dine out in one of the town’s fine restaurants and have a night on the town. With Diminuendo moored in the marina, you’re free to come and go as you, please.


Day Five: Today, you’ll depart Friday Harbor for beautiful Cyprus Island. Here we will anchor or catch a mooring ball in one of the many coves on the island. Here you can enjoy beautiful paddling and beach combing on the isolated beaches. You can also consider a hike up to Eagle Cliff, which offers a spectacular panorama of the San Juan archipelago.

Day Six: Relax and enjoy your cruise back to the dock in Bellingham. We usually arrive in port in the early afternoon unless you needed to return early. Please let your crew know if you require an early disembarkation time back in Bellingham.

Alas, all good things must come to an end. We trust that your time aboard Diminuendo has created lasting memories. We hope to welcome you aboard again soon!

Alternative Destinations

When you and your party book the entire boat for a private cruise charter, you have the added flexibility of fine-tuning your crewed boat charter vacation six-day itinerary, creating a week tailored to your personal preferences. Some variations on your private charter cruise could include the following:

Lopez Island: Lopez Island offers many tantalizing possibilities, such as Spenser Spit State Park, Watmough Bay, or Mackaye Harbor. With its relatively flat terrain, Lopez Island is an excellent choice for bicycling. Bikes are available for rent, but the delivery of your bikes to our destination must be made in advance.

Orcas Island: The largest of the islands (depending on who you talk to) is Orcas Island. It offers a few possible destinations.

Deer Harbor is a small, intimate marina with several small restaurants.

Rosario Resort in East Sound offers a luxurious spa and a swimming pool, and in the evenings, it is common for the resort manager to play the Hammond pipe organ in what was once the Moran mansion. Cascade Lake is a short hike from the resort.

Due to its size, fully experiencing the island will require a vehicle. A rental car can be dropped off at a pre-determined destination if arranged in advance. Or you may take a guided tour with one of the local operators.

You’ll definitely want to get to the top of Mount Constitution in Moran State Park. Atop its 2400-foot peak is a stone observation tower built by the Civilian Conservation Corp (CCC) during the great depression. From there, you’ll be able to take in the full panorama. You may recognize some of the islands you’ve visited.


Looking for a San Juan Islands chartered sailboat vacation?

Look no further than Northwest Sailing Adventures!